I have this same problem, although the behavior that I'm seeing is that, under shuffle, the last track will play, and then #1 (i.e., not #2), and _then_ #2, #3, etc.

As an added tidbit that might help some developer diagnose the problem (without their being able to re-create it themselves), I noticed that my random sort doesn't work, either.

Specifically, in the Winamp Classic skin, when I click "MiSC" and then click "SORT LIST" and then select "Randomize list", what ends up happening is that whatever track is in last position in the playlist gets moved up to the first position (and that's it; no other tracks change position).

I have a pet theory that what caused this was some kind of corruption to my computer's random number-generation library(s), because I first noticed this problem after a situation where I had to power down the computer ungracefully (just yanking power, basically); after the computer started back up, I noticed this problem w/ Winamp and some other problems perhaps related to encryption / random numbers (e.g., password protection in MS Excel doesn't work any more; cookies and other personalized settings in web browsers have gone flakey now; and so forth).